2019-12-27 10:37:06
Fan Teng,a, b Weiming Hu,a, b Huaanzi Hu,a, b Shuang Luo,a, b,* and Qiang Zhua, b,* a State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of
Sciences, 190 Kaiyuan Avenue, Guangzhou 510530 People’s Republic of China
Fax: (+86) 20-3201-5299
E-mail: [email protected]; [email protected] b University of Chinese Academy of Sciences, No. 19(A) Yuquan Road, Shijingshan District, Beijing 100049, Peoples
Republic of China
Manuscript received: December 4, 2018; Revised manuscript received: January 9, 2019;
Version of record online: January 29, 2019
Supporting information for this article is available on the WWW under https://doi.org/10.1002/adsc.201801623
Nonfunctionalized isocyanide (RNC) usually serves as a C1 building block through a,a-difunctinalization of the terminal divalent isocyano carbon to get a C=N or C=O containing product in which the isocyano carbon turns to the “normal” valent state.[1] In this process, the pending group R in isocyanide does not participate in the reaction by itself; and even in some cases, it is hydrolyzed simultaneously or during the following transformations. In recent years, functionalized isocyanides, by incorporating functionalities capable of trapping various isocyano-derived intermediates intramolecularly, have attracted extensive attention in the synthesis of a myriad of nitrogen heterocyclic motifs.[2]
By taking this strategy, almost all atoms in isocyanide are maintained in the final cyclized products, which is not only highly atom economic but also efficient in generating molecular complexity and structural diversity. For instance, in palladium-catalyzed imidoylative annulation of functionalized isocyanides, the key imidoyl Pd(II) intermediates formed by migratory insertion of isocyanide to a Pd(II) species could be captured by various intramolecular functional groups,[3] such as carbonyl oxygen of amides,[3a–b] aromatic CH bonds,[3c–h] alkenes,[3i–j] and alkynes,[3k–l] leading to heterocyclic compounds such as oxazoles, phenanthridines, cyclic ketoimines, and indole-fused derivatives. Intramolecular trapping of the imidoyl radical intermediates is another important application of functionalized isocyanides, which has been widely studied in the synthesis of phenanthridine, quinoxaline, benzoimidazole analogues and so on.[4]
However, when a functionalized isocyanide contains multiple reactive sites to terminate imidoyl intermediates, selective annulation is a challenging task with very limited successful examples.[3d,g–h] Recently, a ligand-controlled site-selective C(sp2)H cycloimidoylation process was realized starting from 2-isocyano-2,3-diarylpropanoates to deliver six-membered 3,4-dihydroisoquinolines and five-membered 1,1-disubstituted 1H-isoindoles (a, Scheme 1).[3h] Meanwhile, by discriminating two symmetric C(sp2)H bonds, enantioselective construction of central and planar chiral compounds were accomplished by Pd-catalyzed cycloimidoylations in the presence of SPINOL-derived phosphoramidites (b).[3d,g] However, in the aforementioned reactions, the selectivity was taking place between the same type of functionality, C(sp2)H bonds. We envisioned that 2-(2-isocyanophenyl)-1H-indoles, a class of functionalized isocyanides containing both CH and NH bonds capable of imidoylation, would be ideal substrates to study chemo-selective cycloimidoylation between different types of functionalities (c). Correspondingly, the construction of substituted 1H-indolo[3,2-c]quinoline and indolo[1,2-c]quinazoline derivatives will be expected through CH and NH bond cycloimidoylation, respectively. Importantly, both of these motifs are frequently found in natural products and biologically active molecules.
Inspired by recent advances in cascade radical addition/cyclization of radical intermediates with 2-isocyano-1,1’-biphenyls,[6] we tested the hypothesis of chemo-selective cycloimidoylation using 2-(2 isocyanophenyl)-1H-indole 1 a as a representative model substrate and PhB(OH)2 2 a as a phenyl radical source in the presence of Mn(acac)3 in DCE at 808C under Ar. Delightfully, 6-phenyl 11H-indolo[3,2-c]quinoline 4 a, generated from C(sp2)H cycloimidoylation, was isolated selectively in 54% yield (entry 1, Table 1).
The other possible cyclization product 5 a was hardly detected. The yield of 4 a was improved to 62% when MeCN was used as a solvent (entry 2). Elevating the reaction temperature to 1008C was proven to be beneficial (73%, entry 3). Finally, 4 a could be isolated in 82% yield with 3.0 equivalents of PhB(OH)2 and Mn(acac)3. Then, the reaction of 1 a with PhI 3 a under palladium catalysis was investigated. 6-Phenyl indolo [1,2-c]quinazoline 5 a, derived from NH bond cycloimidoylation, was formed exclusively under reaction conditions involving Pd(OAc)2, PPh3 and Cs2CO3 in toluene at 80 8C under Ar (56%, entry 4). When Cs2CO3 was replaced by CsOPiv, the yield of 5 a was increased remarkably to 73%. To avoid handling hygroscopic CsOPiv, in-situ formation of CsOPiv by mixing Cs2CO3 and PivOH was preferred, which gave a slightly improved yield of 5 a (77%, entry 6).
Notably, under all of the above conditions for Pd catalysis, cycloimidolylation at the C-3 position of indole was suppressed, and 4 a was only detected in trace amount. This result might be assigned to the
coordination ability of the NH free nitrogen of indole.[7]
With the optimal reaction conditions for selective formation of 4 a established, the scope of arylboronic acids 2 in this Mn-mediated radical cyclization was first explored (Scheme 2). 6-Aryl 11H-indolo[3,2-c]
quinolines bearing electron-donating (4 b–4 d, 4 h–4 j) or electron-withdrawing groups (4 e–4 g) on 6-aryl could be formed in moderate to good yields (41–87%) with the corresponding arylboronic acids as the aryl source. Functionalities including Cl, Br, and acetyl tolerated well under the reaction conditions. Notably, amino substituted derivative 4 j which showed good activity against Mycobacterium tuberculosis according to our previous report (MIC=2.5 mg/mL),[5f] could be obtained in 42% yield. In addition, the bulky 1-naphthyl group could also be installed at the C6 position of 11H-indolo[3,2-c]quinoline scaffold in 64% yield (4 k). Secondary alkylboronic acids could also provide the corresponding 6-alkyl substituted products in moderate yields (4l, 4m). However, the reaction with 1-butanylboronic acid as a radical source could not deliver the corresponding product.
Then, studies by varying substitutents on 2-(2-isocyanophenyl)-1H-indoles 1 were carried out (Scheme 3). Preliminary results showed that electronwithdrawing groups (F, Cl, Br) on the indole moiety
gave slightly better results than electron-donating methyl (4 o–4 q vs. 4 n and 4 r). When 2-(2-isocyanophenyl)-1-methyl-1H-indole was subjected to the reaction conditions, the annulation product 4 s was isolated in 65% yield.
Next, the feasibility for indolo[1,2-c]quinazoline formation under Pd catalysis was investigated (Scheme 4). In general, electron-deficient ArI gave better yields of 5 than those of electron-rich ones. For example, 4-iodobenzonitrile and 4-iodoanisole delivered the corresponding products in 80% (5 f) and 56% (5 e) yields, respectively. However, when 2-iodobenzonitrile was applied, the annulated product 5 c was generated in only 47% yield, indicating the negative effect of steric hindrance of iodide. Remarkably, 3-iodopyridine and 2-iodothiophene could also afford the heteroaromatic substituted products 5i and 5 j in moderate yields. In addition, both of the reactions for selective annulation could be scaled up using 1 mmol of 1 a in almost identical yields of 4 a and 5 a, verifying
the practicality of the methods.
Finally, the tolerance of functionalized isocyanides was tested in reactions with 3 a, and the results were summarized in Scheme 5. 2-(2-Isocyanophenyl)-1Hindoles containing different substituents on the indole moiety were investigated, and the desired NH cycloimidoylation products 5 k–5 p were generated in 51–76% yields. When 2-(2-isocyanophenyl)-7-methyl-1H indole bearing a methyl group adjacent to the indolo NH was used, the reaction proceeded equally well to produce 5 p in 68% yield.
This kind of chemo-selective CH or NH imidoylative annulation was also applicable to other structurally similar isocyanide. When 2-(2-isocyanophenyl)-1H-pyrrole 6 was subjected to both aforementioned reactions, 4-phenyl-11H-pyrrolo[3,2-c]quinoline 7 and 5-phenylpyrrolo[1,2-c]quinazoline 8 could be obtained in moderate yields and good selectivity following the pathways of CH and NH cycloimidoylation, respectively (1, Scheme 6). In addition, CH cycloimidoylation of 1 a with other radical species generated from 1,4-dioxane,[7g] Togni’s reagent[7a] and diphenylphosphine oxide[7q,8] took place smoothly to give C6 diversified 11H-indolo[3,2-c]quinolines 9–11 in yields ranging from 58% to 64% (2–4).
In conclusion, we reported a chemo-selective cycloimidoylation of 2-(2-isocyanophenyl)-1H-indoles, a class of functionalized isocyanides containing both aromatic CH and indolo NH functionalities capable of trapping imidoyl intermediates. Under radical conditions, homolytic aromatic substitution (HAS) of the imidoyl radical intermediate takes place preferentially regardless of radical sources, generating C6 diversified 11H-indolo[3,2-c]quinolines. In contrast, NH cycloimidoylation dominates the fate of imidoyl palladium(II) intermediate, leading to 6-aryl indolo [1,2-c]quinazolines exclusively. Both of the indolefused scaffolds are frequently found in promising drug candidates and natural products. The current research expands the synthetic application of functionalized isocyanides in diversified N-heterocycle synthesis.
Experimental Section
Annulation toward 6-ary-11H-indolo[3,2-c]quinoline: Under Ar, a 20 mL Schlenk tube equipped with a stirring bar was charged with isocyanide 1 or 6 (0.1 mmol), ArB(OH)2 (0.3 mmol), Mn(acac)3 (105.8 mg, 0.3 mmol), MeCN (2 mL). The tube was sealed with a Teflon lined cap. The reaction mixture was stirred at 100 8C for 24 h in an oil bath. After completion of the reaction (as monitored by TLC), the reaction mixture was concentrated in vacuum, and the product was purified by flash column chromatography on silica gel with petroleum ether-EtOAc as the eluent to give the desired product.
Annulation toward 6-arylindolo[1,2-c]quinazoline:
An oven-dried 25 mL Schlenk tube charged with Pd(OAc)2 (0.01 mmol, 2.2 mg), PPh3 (0.02 mmol, 5.2 mg) and Cs2CO3(0.12 mmol, 39.0 mg) was vacuumed and refilled with Ar for 3 times. Then, a solution of ArI (0.12 mmol, 1.2 equiv.), PivOH (0.12 mmol, 14.0 mL, 1.2 equiv.) in 1.0 mL of toluene was added by syringe and the tube was placed in an 80 8C oilbath. A solution of isocyanide 1 or 6 (0.1 mmol, 1.0 equiv.) in 1.0 mL of toluene was added dropwise with a syringe pump to the reaction mixture. The addition was finished within 1 h. The crude reaction mixture was extracted with EA (2 mL 33) and washed with brine (5 mL). The organic phase was concentrated in vacuo and the residue was purified by silica gel flash column chromatography to afford the corresponding products.
Acknowledgements
We are grateful to the National Natural Science Foundation of China (NNSFC) (21532009, 21772198, and 21871268) for financial support.
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5-(Methylcarbamoyl)thiophene-3-sulfonyl chlorideCatalog No.:AA007VTJ CAS No.:1060817-61-9 MDL No.:MFCD11053992 MF:C6H6ClNO3S2 MW:239.6997 |
4-(Isoxazol-5-yl)thiophene-2-sulfonyl chlorideCatalog No.:AA0084BM CAS No.:1060817-63-1 MDL No.:MFCD11054004 MF:C7H4ClNO3S2 MW:249.6946 |
3-Methyl-4-oxo-3,4-dihydro-7-quinazolinecarboxylic acidCatalog No.:AA00993A CAS No.:1060817-67-5 MDL No.:MFCD11054010 MF:C10H8N2O3 MW:204.1821 |
3-(2-Bromo-4-methylphenyl)-1,3-oxazolidin-2-oneCatalog No.:AA007E1O CAS No.:1060817-68-6 MDL No.:MFCD11054012 MF:C10H10BrNO2 MW:256.0959 |
5-Bromo-4-methyl-2-(4H-1,2,4-triazol-4-yl)pyridineCatalog No.:AA008V6C CAS No.:1060817-70-0 MDL No.:MFCD11054014 MF:C8H7BrN4 MW:239.0720 |
N-Methyl-1-(4-methyl-1,2,3-thiadiazol-5-yl)methanamineCatalog No.:AA007E1N CAS No.:1060817-72-2 MDL No.:MFCD11054019 MF:C5H9N3S MW:143.2101 |
3-Bromo-2-methyl-6-(4H-1,2,4-triazol-4-yl)pyridineCatalog No.:AA008VJ7 CAS No.:1060817-73-3 MDL No.:MFCD11054020 MF:C8H7BrN4 MW:239.0720 |
5-(3-Methylisoxazol-5-yl)furan-2-sulfonyl chlorideCatalog No.:AA0084BL CAS No.:1060817-75-5 MDL No.:MFCD11054021 MF:C8H6ClNO4S MW:247.6555 |
3-[(2-FURYLMETHYL)THIO]-1-PROPANAMINECatalog No.:AA007VTI CAS No.:1060817-77-7 MDL No.:MFCD10694535 MF:C8H13NOS MW:171.2599 |
(+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-olCatalog No.:AA008TK7 CAS No.:106083-71-0 MDL No.:MFCD10565921 MF:C13H19Cl2NO2 MW:292.2015 |
PROPAN-2-YL CYCLOPENTANECARBOXYLATECatalog No.:AA01DX6U CAS No.:106083-73-2 MDL No.:MFCD21101244 MF:C9H16O2 MW:156.2221 |
2-(Bromomethyl)-1,3-benzothiazoleCatalog No.:AA007VNV CAS No.:106086-78-6 MDL No.:MFCD00461195 MF:C8H6BrNS MW:228.1089 |
(S)-3-Bromo-2-hydroxy-2-methylpropanoic acidCatalog No.:AA003BM1 CAS No.:106089-20-7 MDL No.:MFCD09750950 MF:C4H7BrO3 MW:183.0006 |
(S)-4,5,6,7-Tetrahydro-2,6-benzothiazolediamineCatalog No.:AA003CJJ CAS No.:106092-09-5 MDL No.:MFCD07368003 MF:C7H11N3S MW:169.2473 |
(+)-(6R)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazoleCatalog No.:AA007DLJ CAS No.:106092-11-9 MDL No.:MFCD07369986 MF:C7H11N3S MW:169.2473 |
(E)-2-(1-Butenyl)-1,3,2-benzodioxaboroleCatalog No.:AA008WMB CAS No.:106094-36-4 MDL No.:MFCD27977783 MF:C10H11BO2 MW:174.0041 |
4-(1,3-dithiolan-2-yl)-N-(3-hydroxypyridin-2-yl)benzamideCatalog No.:AA019RXJ CAS No.:1060968-92-4 MDL No.:MFCD11774214 MF:C15H14N2O2S2 MW:318.4139 |
6-Bromo-5-methoxy-1h-indoleCatalog No.:AA008XNT CAS No.:106103-36-0 MDL No.:MFCD11848542 MF:C9H8BrNO MW:226.0699 |
Benzene, 1-chloro-3-(isocyanomethyl)-Catalog No.:AA007VND CAS No.:106106-81-4 MDL No.:MFCD26620466 MF:C8H6ClN MW:151.5929 |
Methyl 2-[(chloroacetyl)amino]-3-phenylpropanoateCatalog No.:AA00HAP9 CAS No.:106109-98-2 MDL No.:MFCD00548259 MF:C12H14ClNO3 MW:255.6975 |
1-[2-(dimethylamino)ethyl]-2,3-dihydro-1H-indole-2,3-dioneCatalog No.:AA01BB5R CAS No.:106110-60-5 MDL No.:MFCD00455172 MF:C12H14N2O2 MW:218.2518 |
L-Serine, N-[(4-chlorophenyl)sulfonyl]-Catalog No.:AA007VN8 CAS No.:106111-13-1 MDL No.:MFCD02230141 MF:C9H10ClNO5S MW:279.6974 |
17b-Hydroxy-3-oxo-9-norpregna-5(10),9(11)-diene-21-nitrileCatalog No.:AA008UH9 CAS No.:106111-42-6 MDL No.:MFCD22194425 MF:C20H25NO2 MW:311.4180 |
(2E,5E)-2,5-bis[(4-chlorophenyl)methylidene]cyclopentan-1-oneCatalog No.:AA00ISTN CAS No.:106115-45-1 MDL No.:MFCD00121539 MF:C19H14Cl2O MW:329.2199 |
Methyl 2-oxopiperidine-3-carboxylateCatalog No.:AA009T01 CAS No.:106118-94-9 MDL No.:MFCD03410215 MF:C7H11NO3 MW:157.1671 |
5-Bromo-1,3-benzenediolCatalog No.:AA003MI9 CAS No.:106120-04-1 MDL No.:MFCD16293393 MF:C6H5BrO2 MW:189.0067 |
4-[2-[1-(4-Methylphenyl)ethylidene]hydrazinyl]benzenesulfonamideCatalog No.:AA01DZEN CAS No.:1061214-06-9 MDL No.: MF:C15H17N3O2S MW:303.3794 |
4-[[3-(4-Methylphenyl)-3-oxo-1-(trifluoroMethyl)propylidene]aMino]benzenesulfonaMideCatalog No.:AA008VV4 CAS No.:1061214-09-2 MDL No.:MFCD32069550 MF:C17H15F3N2O3S MW:384.3728 |
4-Fluoro-2-(hydroxymethyl)phenylboronic acidCatalog No.:AA003862 CAS No.:1061223-45-7 MDL No.:MFCD22205750 MF:C7H8BFO3 MW:169.9460 |
(5S,8S,14S,17S,20S)-14,17-Dibenzyl-5-carbamoyl-20-(carboxymethyl)-8-isobutyl-15-methyl-7,10,13,16,19,22-hexaoxo-2-thia-6,9,12,15,18,21-hexaazapentacosan-25-oic acidCatalog No.:AA00842I CAS No.:106128-89-6 MDL No.:MFCD00076799 MF:C40H55N7O11S MW:841.9700 |
Methyl 2-(4-bromophenyl)-3-methylbutanoateCatalog No.:AA0093IP CAS No.:1061284-70-5 MDL No.:MFCD16340133 MF:C12H15BrO2 MW:271.1503 |
(2E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-oneCatalog No.:AA007VIU CAS No.:106129-86-6 MDL No.:MFCD00172108 MF:C11H13NO2 MW:191.2264 |
3,6-Dichloro-1,2,4,5-tetrazineCatalog No.:AA00363M CAS No.:106131-61-7 MDL No.:MFCD22042702 MF:C2Cl2N4 MW:150.9542 |
Debio 0932 ,CUDC-305Catalog No.:AA008TLW CAS No.:1061318-81-7 MDL No.:MFCD18633209 MF:C22H30N6O2S MW:442.5776 |
3-Bromophenylglyoxal hydrateCatalog No.:AA008UDL CAS No.:106134-16-1 MDL No.:MFCD08448029 MF:C8H7BrO3 MW:231.0434 |
Pnd-1186Catalog No.:AA008TGB CAS No.:1061353-68-1 MDL No.:MFCD28125506 MF:C25H26F3N5O3 MW:501.5008 |
6-Chloro-4-iodonicotinonitrileCatalog No.:AA007DK0 CAS No.:1061357-83-2 MDL No.:MFCD16658125 MF:C6H2ClIN2 MW:264.4510 |
6-Bromo-4-iodonicotinonitrileCatalog No.:AA00HAPB CAS No.:1061357-87-6 MDL No.:MFCD16657907 MF:C6H2BrIN2 MW:308.9020 |
2-Bromo-5-fluoro-4-iodopyridineCatalog No.:AA007DJZ CAS No.:1061357-89-8 MDL No.:MFCD15143627 MF:C5H2BrFIN MW:301.8830 |
2-((2-Chloro-5-(trifluoromethyl)pyridin-4-yl)amino)-N-methylbenzamideCatalog No.:AA008W0Y CAS No.:1061358-71-1 MDL No.:MFCD30186653 MF:C14H11ClF3N3O MW:329.7048 |
2-Chloro-5-(trifluoromethyl)pyridin-4-amineCatalog No.:AA0095DD CAS No.:1061358-78-8 MDL No.:MFCD16658126 MF:C6H4ClF3N2 MW:196.5576 |
(S)-2-Pyridylthio cysteamine, HClCatalog No.:AA0035ZT CAS No.:106139-15-5 MDL No.:MFCD01863453 MF:C7H11ClN2S2 MW:222.7586 |
2-bromophenyl 3-chloro-2,2-dimethylpropanoateCatalog No.:AA01BF7O CAS No.:106141-11-1 MDL No.:MFCD28118545 MF:C11H12BrClO2 MW:291.5688 |
3,3-dimethyl-3,4-dihydro-2H-1-benzopyran-4-oneCatalog No.:AA01EJUD CAS No.:106141-28-0 MDL No.:MFCD20482573 MF:C11H12O2 MW:176.2118 |
4-N-PropoxyphthalonitrileCatalog No.:AA003LUS CAS No.:106144-18-7 MDL No.:MFCD00059102 MF:C11H10N2O MW:186.2099 |
1-[4-(Bromomethyl)piperidin-1-yl]-2,2-dimethylpropan-1-oneCatalog No.:AA01A66A CAS No.:1061458-45-4 MDL No.:MFCD11612761 MF:C11H20BrNO MW:262.1866 |
N-(3-OXO-3-PYRROLIDIN-1-YLPROPYL)-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIO+Catalog No.:AA01ELN2 CAS No.:1061503-78-3 MDL No.:MFCD10928780 MF:C17H24N2O2S MW:320.4497 |
(Ferrocenylmethyl)trimethylammonium bromideCatalog No.:AA003BYH CAS No.:106157-30-6 MDL No.:MFCD00059981 MF:C14H20BrFeN MW:338.0643 |
1-(2-Aminopyrimidin-4-yl)ethanoneCatalog No.:AA008RC7 CAS No.:106157-82-8 MDL No.:MFCD09263814 MF:C6H7N3O MW:137.1393 |
4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinoline-6-sulfonyl chlorideCatalog No.:AA01C80L CAS No.:1061596-54-0 MDL No.:MFCD11846987 MF:C11H12ClNO3S MW:273.7359 |
2-[[2-(2,6-Dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]oxy]aceticacidCatalog No.:AA01ENF7 CAS No.:1061605-21-7 MDL No.:MFCD31560477 MF:C15H12N2O7 MW:332.2650 |
4-(3-Nitrophenoxy)benzamideCatalog No.:AA00HAPH CAS No.:106164-01-6 MDL No.:MFCD14583107 MF:C13H10N2O4 MW:258.2295 |
7-fluoroquinoline-6-carboxylic acidCatalog No.:AA01BI1Z CAS No.:1061650-21-2 MDL No.:MFCD18072496 MF:C10H6FNO2 MW:191.1585 |
8-Fluoroquinoline-6-carboxylic acidCatalog No.:AA0095SA CAS No.:1061650-25-6 MDL No.:MFCD20660878 MF:C10H6FNO2 MW:191.1585 |
[3-(2-fluorophenoxy)phenyl]methanamineCatalog No.:AA01C5B2 CAS No.:1061651-05-5 MDL No.:MFCD19613864 MF:C13H12FNO MW:217.2389 |
2-{3-[(3-methylbut-2-en-1-yl)oxy]phenyl}acetic acidCatalog No.:AA01C3A1 CAS No.:1061652-65-0 MDL No.:MFCD14658997 MF:C13H16O3 MW:220.2643 |
(R)-2-(Piperidin-2-yl)pyridineCatalog No.:AA008VQ7 CAS No.:1061659-74-2 MDL No.:MFCD09257392 MF:C10H14N2 MW:162.2316 |
2-(4-Formylphenyl)-5-propyl-1,3,4-oxadiazoleCatalog No.:AA00HAPI CAS No.:1061671-93-9 MDL No.:MFCD19104825 MF:C12H12N2O2 MW:216.2359 |
2-(But-1-yl)-5-(4-formylphenyl)-1,3,4-oxadiazoleCatalog No.:AA009N32 CAS No.:1061672-63-6 MDL No.:MFCD18909698 MF:C13H14N2O2 MW:230.2625 |
4-(2,2-dimethylpyrrolidin-1-yl)piperidineCatalog No.:AA01DUVG CAS No.:1061682-59-4 MDL No.:MFCD18295240 MF:C11H22N2 MW:182.3058 |
4-methyl-4-(pyrrolidin-1-yl)piperidineCatalog No.:AA01BQX7 CAS No.:1061683-29-1 MDL No.:MFCD26938770 MF:C10H20N2 MW:168.2792 |
N-Methoxy-2-nitrobenzenesulfonamideCatalog No.:AA00HAPJ CAS No.:1061696-67-0 MDL No.:MFCD18072513 MF:C7H8N2O5S MW:232.2138 |
tert-Butyl 8-oxo-3,9-diazaspiro[5.5]undecane-3-carboxylateCatalog No.:AA0096RM CAS No.:1061731-86-9 MDL No.:MFCD13184372 MF:C14H24N2O3 MW:268.3520 |
AcetaMide, N-[2-(3,5-diMethyl-1H-pyrazol-1-yl)-6-[6-(4-Methoxy-1-piperidinyl)-2-pyridinyl]-4-pyriMidinyl]-Catalog No.:AA0097HI CAS No.:1061747-72-5 MDL No.:MFCD18642652 MF:C22H27N7O2 MW:421.4955 |
6,7-Dimethyl-2-(5-methylthiophen-2-yl)quinoline-4-carboxylic acidCatalog No.:AA01BC7T CAS No.:1061996-80-2 MDL No.:MFCD28714760 MF:C17H15NO2S MW:297.3715 |
5-(4-bromophenoxy)-1-methyl-4-nitro-1H-imidazoleCatalog No.:AA01A0CW CAS No.:1061999-85-6 MDL No.:MFCD07993703 MF:C10H8BrN3O3 MW:298.0928 |
5-Cholesten-3β-ol caproateCatalog No.:AA003OSP CAS No.:1062-96-0 MDL No.:MFCD00037707 MF:C33H56O2 MW:484.7965 |
Methyl 4-(4-oxobutyl)benzoateCatalog No.:AA008U4N CAS No.:106200-41-3 MDL No.:MFCD09753703 MF:C12H14O3 MW:206.2378 |
Ethyl 4-(trifluoromethyl)-1,3-thiazole-5-carboxylateCatalog No.:AA00950O CAS No.:106203-24-1 MDL No.:MFCD17170046 MF:C7H6F3NO2S MW:225.1882 |
1-(Isopropylsulfonyl)piperazine hydrochlorideCatalog No.:AA01AQSE CAS No.:1062059-60-2 MDL No.:MFCD16661023 MF:C7H17ClN2O2S MW:228.7401 |
tert-Butyl 4-(5-chloro-6-oxo-1-phenyl-1,6-dihydropyridazin-4-yl)piperazine-1-carboxylateCatalog No.:AA00HAPM CAS No.:1062070-07-8 MDL No.:MFCD21332877 MF:C19H23ClN4O3 MW:390.8639 |
1-(Heptadecafluorooct-1-yl)-4-vinylbenzeneCatalog No.:AA009T1K CAS No.:106209-21-6 MDL No.:MFCD17168266 MF:C16H7F17 MW:522.1996 |
N-[(3R)-Piperidin-3-yl]benzamideCatalog No.:AA00HAPO CAS No.:1062136-14-4 MDL No.:MFCD24553221 MF:C12H16N2O MW:204.2682 |
AMINOPROPYL TERMINATED POLYDIMETHYLSILOXANECatalog No.:AA008UR9 CAS No.:106214-84-0 MDL No.:MFCD00241456 MF:C7H21NO2Si2 MW:207.4181 |
Way-600Catalog No.:AA008YUM CAS No.:1062159-35-6 MDL No.:MFCD22419019 MF:C28H30N8O MW:494.5908 |
Wye-687Catalog No.:AA008THV CAS No.:1062161-90-3 MDL No.:MFCD22417086 MF:C28H32N8O3 MW:528.6055 |
4-[6-[4-[[(cyclopropylamino)carbonyl]amino]phenyl]-4-(4-morpholinyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylicacid,methylesterCatalog No.:AA01EPJT CAS No.:1062169-46-3 MDL No.: MF:C26H32N8O4 MW:520.5835 |
WYE-354Catalog No.:AA008SQ1 CAS No.:1062169-56-5 MDL No.:MFCD18074514 MF:C24H29N7O5 MW:495.5310 |
4-[6-[4-[[[[4-(hydroxymethyl)phenyl]amino]carbonyl]amino]phenyl]-4-(4-morpholinyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylicacid,methylesterCatalog No.:AA01EPJU CAS No.:1062172-60-4 MDL No.: MF:C30H34N8O5 MW:586.6416 |
5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolineCatalog No.:AA007DEV CAS No.:1062174-44-0 MDL No.:MFCD16995801 MF:C14H20BNO2 MW:245.1251 |
Methyl2,3-di-O-methyl-6-O-(phenylmethyl)-a-D-glucopyranosideCatalog No.:AA008YJB CAS No.:106220-89-7 MDL No.:MFCD15145034 MF:C16H24O6 MW:312.3582 |
Palladium(II) pivalateCatalog No.:AA003TGJ CAS No.:106224-36-6 MDL No.:MFCD16038138 MF:C10H18O4Pd MW:308.6675 |
Ro 3280Catalog No.:AA008TGL CAS No.:1062243-51-9 MDL No.:MFCD22665717 MF:C27H35F2N7O3 MW:543.6087 |
2-Chloro-9-cyclopentyl-7,7-difluoro-8,9-dihydro-5h-pyrimido[4,5-b][1,4]diazepin-6(7h)-oneCatalog No.:AA00HAPS CAS No.:1062246-01-8 MDL No.:MFCD25542099 MF:C12H13ClF2N4O MW:302.7076 |
2-Chloro-9-cyclopentyl-7,7-difluoro-5-methyl-8,9-dihydro-5h-pyrimido[4,5-b][1,4]diazepin-6(7h)-oneCatalog No.:AA00HAPT CAS No.:1062246-03-0 MDL No.:MFCD25542098 MF:C13H15ClF2N4O MW:316.7342 |
MK6-83Catalog No.:AA009504 CAS No.:1062271-24-2 MDL No.:MFCD10736412 MF:C16H20N2O2S2 MW:336.4722 |
5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazoleCatalog No.:AA019UF9 CAS No.:1062295-85-5 MDL No.:MFCD03422575 MF:C7H7F3N2 MW:176.1391 |
4-(Methylsulfonyl)-1H-pyrazol-3-amineCatalog No.:AA0095AM CAS No.:106232-38-6 MDL No.:MFCD16620087 MF:C4H7N3O2S MW:161.1823 |
4-methanesulfonyl-1h-pyrazol-5-amine hydrochlorideCatalog No.:AA01EI1F CAS No.:106232-39-7 MDL No.:MFCD31457267 MF:C4H8ClN3O2S MW:197.6432 |
4-(Quinolin-4-yl)-1H-pyrazol-3-amineCatalog No.:AA0039G0 CAS No.:1062368-21-1 MDL No.:MFCD24627430 MF:C12H10N4 MW:210.2346 |
6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidineCatalog No.:AA008TEI CAS No.:1062368-24-4 MDL No.:MFCD17169988 MF:C25H22N6 MW:406.4824 |
5-[6-(4-Methoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinolineCatalog No.:AA00397H CAS No.:1062368-49-3 MDL No.:MFCD28099805 MF:C22H16N4O MW:352.3886 |
4-(6-(4-(Piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)quinoline hydrochlorideCatalog No.:AA008TEJ CAS No.:1062368-62-0 MDL No.:MFCD17392570 MF:C25H23ClN6 MW:442.9433 |
Methyl 6-bromopyrazolo[1,5-a]pyridine-3-carboxylateCatalog No.:AA007VA1 CAS No.:1062368-70-0 MDL No.:MFCD15474972 MF:C9H7BrN2O2 MW:255.0681 |
Methyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylateCatalog No.:AA0092FX CAS No.:1062368-71-1 MDL No.:MFCD19703856 MF:C9H7BrN2O2 MW:255.0681 |
6-(piperidin-3-ylamino)pyridine-3-carbonitrileCatalog No.:AA01BU78 CAS No.:1062369-35-0 MDL No.:MFCD18330340 MF:C11H14N4 MW:202.2557 |
6-Chloro-3-[(hydroxyimino)methyl]pyridin-2-amineCatalog No.:AA01BD8U CAS No.:1062369-45-2 MDL No.:MFCD28064223 MF:C6H6ClN3O MW:171.5843 |
3-benzoylpyridine-2-carboxylic acid hydrochlorideCatalog No.:AA00IS2K CAS No.:106240-68-0 MDL No.:MFCD18904328 MF:C13H10ClNO3 MW:263.6764 |
1-[(2-aminophenyl)methyl]imidazolidin-2-oneCatalog No.:AA01A4PX CAS No.:1062404-58-3 MDL No.:MFCD09802811 MF:C10H13N3O MW:191.2297 |
2-(6-methyl-1H-1,3-benzodiazol-2-yl)benzoic acidCatalog No.:AA01C2YG CAS No.:106242-28-8 MDL No.:MFCD08815731 MF:C15H12N2O2 MW:252.2680 |
ThioperamideCatalog No.:AA0035M7 CAS No.:106243-16-7 MDL No.:MFCD00083209 MF:C15H24N4S MW:292.4429 |
4-(1H-Imidazole-4(5)-yl) piperidineCatalog No.:AA008R12 CAS No.:106243-23-6 MDL No.:MFCD02179572 MF:C8H13N3 MW:151.2089 |
Dichloro[1,3-bis(diphenylphosphino)propane]iron(II)Catalog No.:AA01FR4X CAS No.:106245-43-6 MDL No.:MFCD29037156 MF:C27H28Cl2FeP2++ MW:541.2097 |
4,4'-Methylenebis(3-chloro-2,6-diethylaniline)Catalog No.:AA0083Z5 CAS No.:106246-33-7 MDL No.:MFCD00071551 MF:C21H28Cl2N2 MW:379.3664 |
H-Beta-tBu-DL-Ala-OHCatalog No.:AA008UGU CAS No.:106247-35-2 MDL No.:MFCD00066078 MF:C10H13NO4 MW:211.2145 |
TRIPHENYLOLMETHANE TRIGLYCIDYL ETHER 2,6-TOLYLENE DIISOCYANATE ADDUCTCatalog No.:AA008RUE CAS No.:106253-69-4 MDL No.:MFCD00192548 MF:C37H34N2O8 MW:634.6745 |
(3R,4R)-1-Benzyl-N,4-dimethylpiperidin-3-amine dihydrochlorideCatalog No.:AA003898 CAS No.:1062580-52-2 MDL No.:MFCD09864744 MF:C14H24Cl2N2 MW:291.2598 |